CA2549548A1 - Carboxamide derivatives - Google Patents
Carboxamide derivatives Download PDFInfo
- Publication number
- CA2549548A1 CA2549548A1 CA002549548A CA2549548A CA2549548A1 CA 2549548 A1 CA2549548 A1 CA 2549548A1 CA 002549548 A CA002549548 A CA 002549548A CA 2549548 A CA2549548 A CA 2549548A CA 2549548 A1 CA2549548 A1 CA 2549548A1
- Authority
- CA
- Canada
- Prior art keywords
- denotes
- chlorophenyl
- oxo
- urea
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 135
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 108010074860 Factor Xa Proteins 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 239000003112 inhibitor Substances 0.000 claims abstract description 4
- -1 2-oxopiperidin-1-yl Chemical group 0.000 claims description 203
- 150000003839 salts Chemical class 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 67
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 239000012453 solvate Substances 0.000 claims description 41
- 239000004480 active ingredient Substances 0.000 claims description 38
- 125000002950 monocyclic group Chemical group 0.000 claims description 36
- 229920006395 saturated elastomer Polymers 0.000 claims description 35
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 30
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 27
- 125000004434 sulfur atom Chemical group 0.000 claims description 27
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 24
- 239000005977 Ethylene Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052727 yttrium Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000002619 bicyclic group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 208000007536 Thrombosis Diseases 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 239000004202 carbamide Substances 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 208000006011 Stroke Diseases 0.000 claims description 7
- 238000002399 angioplasty Methods 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 208000010125 myocardial infarction Diseases 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 6
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 6
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 206010022562 Intermittent claudication Diseases 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 6
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 208000037803 restenosis Diseases 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- QHRQUMNANPCUMD-MQWQBNKOSA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-2-oxo-1-phenylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(C)CCC1N1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 QHRQUMNANPCUMD-MQWQBNKOSA-N 0.000 claims description 4
- GHKNSJQCAQPBJM-GJICFQLNSA-N 1-(4-chlorophenyl)-3-[(1r)-2-oxo-1-phenyl-2-(4-pyridin-4-ylpiperazin-1-yl)ethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCN(C=2C=CN=CC=2)CC1 GHKNSJQCAQPBJM-GJICFQLNSA-N 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 101150047265 COR2 gene Proteins 0.000 claims description 4
- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- FCXORFGCKHZKBF-VCUSLETLSA-N 1-(4-chlorophenyl)-3-[(1r)-1-(2-chlorophenyl)-2-[4-(1-methyl-2-oxopiperidin-4-yl)piperidin-1-yl]-2-oxoethyl]urea Chemical compound C1C(=O)N(C)CCC1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C(=CC=CC=2)Cl)CC1 FCXORFGCKHZKBF-VCUSLETLSA-N 0.000 claims description 3
- AAABRKAYLIGPET-XMMPIXPASA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(1-methylpiperidin-4-yl)piperidin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1CN(C)CCC1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 AAABRKAYLIGPET-XMMPIXPASA-N 0.000 claims description 3
- IKVJWTGMPITXRY-XMMPIXPASA-N 1-[(1r)-2-(4-benzoylpiperidin-1-yl)-2-oxo-1-phenylethyl]-3-(4-chlorophenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCC(C(=O)C=2C=CC=CC=2)CC1 IKVJWTGMPITXRY-XMMPIXPASA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims description 2
- LSIRKEFJYUWPEZ-XMMPIXPASA-N 1-(4-chlorophenyl)-3-[(1r)-1-(2-chlorophenyl)-2-[4-(1-methylpiperidin-4-yl)piperidin-1-yl]-2-oxoethyl]urea Chemical compound C1CN(C)CCC1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C(=CC=CC=2)Cl)CC1 LSIRKEFJYUWPEZ-XMMPIXPASA-N 0.000 claims description 2
- AJZVPJOTKWRJBB-HSZRJFAPSA-N 1-(4-chlorophenyl)-3-[(1r)-1-(2-chlorophenyl)-2-oxo-2-(4-piperidin-4-ylpiperidin-1-yl)ethyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C(=CC=CC=1)Cl)C(=O)N1CCC(C2CCNCC2)CC1 AJZVPJOTKWRJBB-HSZRJFAPSA-N 0.000 claims description 2
- SZGLHPFQKIUWTC-VZYDHVRKSA-N 1-(4-chlorophenyl)-3-[(1r)-1-(4-hydroxyphenyl)-2-(4-morpholin-4-ylpiperidin-1-yl)-2-oxoethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(O)=CC=C1[C@H](C(=O)N1CCC(CC1)N1CCOCC1)NC(=O)NC1=CC=C(Cl)C=C1 SZGLHPFQKIUWTC-VZYDHVRKSA-N 0.000 claims description 2
- RPRFBYDSXLAIOV-GJFSDDNBSA-N 1-(4-chlorophenyl)-3-[(1r)-1-(4-hydroxyphenyl)-2-[4-(1-methylpiperidin-4-yl)piperidin-1-yl]-2-oxoethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1CN(C)CCC1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC(O)=CC=2)CC1 RPRFBYDSXLAIOV-GJFSDDNBSA-N 0.000 claims description 2
- YEGIAVFRWVOSDX-MQWQBNKOSA-N 1-(4-chlorophenyl)-3-[(1r)-1-(4-hydroxyphenyl)-2-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]-2-oxoethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(C)CCN1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC(O)=CC=2)CC1 YEGIAVFRWVOSDX-MQWQBNKOSA-N 0.000 claims description 2
- RQDSJVQRKZBPEG-GNAFDRTKSA-N 1-(4-chlorophenyl)-3-[(1r)-2-(4-cyclohexylpiperazin-1-yl)-1-(4-hydroxyphenyl)-2-oxoethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(O)=CC=C1[C@H](C(=O)N1CCN(CC1)C1CCCCC1)NC(=O)NC1=CC=C(Cl)C=C1 RQDSJVQRKZBPEG-GNAFDRTKSA-N 0.000 claims description 2
- CZEVCTTZWIOYLT-GNAFDRTKSA-N 1-(4-chlorophenyl)-3-[(1r)-2-(4-cyclohexylpiperazin-1-yl)-2-oxo-1-phenylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCN(C2CCCCC2)CC1 CZEVCTTZWIOYLT-GNAFDRTKSA-N 0.000 claims description 2
- SPCJKMAYAYIMCN-VZYDHVRKSA-N 1-(4-chlorophenyl)-3-[(1r)-2-(4-morpholin-4-ylpiperidin-1-yl)-2-oxo-1-phenylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCC(N2CCOCC2)CC1 SPCJKMAYAYIMCN-VZYDHVRKSA-N 0.000 claims description 2
- LQFJLONKXKWECV-BDQAORGHSA-N 1-(4-chlorophenyl)-3-[(1r)-2-(4-morpholin-4-ylpiperidin-1-yl)-2-oxo-1-thiophen-2-ylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1NC(=O)N[C@@H](C=1SC=CC=1)C(=O)N1CCC(N2CCOCC2)CC1 LQFJLONKXKWECV-BDQAORGHSA-N 0.000 claims description 2
- YMYHXBGCZZKEJR-PIFIWZBESA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(1-methyl-2-oxopiperidin-4-yl)piperidin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1C(=O)N(C)CCC1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 YMYHXBGCZZKEJR-PIFIWZBESA-N 0.000 claims description 2
- KAXJNKLNQQBTJN-XMMPIXPASA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(2-methoxyphenyl)piperazin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound COC1=CC=CC=C1N1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 KAXJNKLNQQBTJN-XMMPIXPASA-N 0.000 claims description 2
- IYDPDDWCGYCEME-PPLJNSMQSA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(4-ethylpiperazin-1-yl)piperidin-1-yl]-2-oxo-1-phenylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(CC)CCN1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 IYDPDDWCGYCEME-PPLJNSMQSA-N 0.000 claims description 2
- NBBGXDYKIJGNLY-XMMPIXPASA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(4-fluorophenoxy)piperidin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1=CC(F)=CC=C1OC1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 NBBGXDYKIJGNLY-XMMPIXPASA-N 0.000 claims description 2
- PJYOTIORUIARDI-HSZRJFAPSA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(4-fluorophenyl)piperazin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1=CC(F)=CC=C1N1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 PJYOTIORUIARDI-HSZRJFAPSA-N 0.000 claims description 2
- YSNQZKXQKUDYSD-MQWQBNKOSA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]-2-oxo-1-phenylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(C)CCN1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 YSNQZKXQKUDYSD-MQWQBNKOSA-N 0.000 claims description 2
- OODVJAHREUUYIA-FGJQBABTSA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]-2-oxo-1-thiophen-2-ylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(C)CCN1C1CCN(C(=O)[C@@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2SC=CC=2)CC1 OODVJAHREUUYIA-FGJQBABTSA-N 0.000 claims description 2
- LSNCSPDFNKYHMC-XMMPIXPASA-N 1-(4-chlorophenyl)-3-[(1r)-2-[4-hydroxy-4-(4-methoxyphenyl)piperidin-1-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1=CC(OC)=CC=C1C1(O)CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)C=2C=CC=CC=2)CC1 LSNCSPDFNKYHMC-XMMPIXPASA-N 0.000 claims description 2
- PBPLZRDAQWTZOP-GNAFDRTKSA-N 1-(4-chlorophenyl)-3-[(1r)-2-oxo-1-phenyl-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCC(N2CCCCC2)CC1 PBPLZRDAQWTZOP-GNAFDRTKSA-N 0.000 claims description 2
- WQHPPKLBOZGFPB-GNAFDRTKSA-N 1-(4-chlorophenyl)-3-[(1r)-2-oxo-1-phenyl-2-(4-piperidin-4-ylpiperidin-1-yl)ethyl]urea;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCC(C2CCNCC2)CC1 WQHPPKLBOZGFPB-GNAFDRTKSA-N 0.000 claims description 2
- OXZYVOYHRPBXIM-JOCHJYFZSA-N 1-(4-chlorophenyl)-3-[(1r)-2-oxo-1-phenyl-2-(4-pyridin-4-ylpiperazin-1-yl)ethyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCN(C=2C=CN=CC=2)CC1 OXZYVOYHRPBXIM-JOCHJYFZSA-N 0.000 claims description 2
- GXQFNKBZIFTYKH-BOXHHOBZSA-N 1-(4-chlorophenyl)-3-[(1r)-2-oxo-2-(4-piperidin-1-ylpiperidin-1-yl)-1-thiophen-2-ylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1NC(=O)N[C@@H](C=1SC=CC=1)C(=O)N1CCC(N2CCCCC2)CC1 GXQFNKBZIFTYKH-BOXHHOBZSA-N 0.000 claims description 2
- ZWZDESFYXWGAAO-UOHPHXQYSA-N 1-(4-chlorophenyl)-3-[(2r,3r)-1-[4-(4-ethylpiperazin-1-yl)piperidin-1-yl]-3-methoxy-1-oxobutan-2-yl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1CN(CC)CCN1C1CCN(C(=O)[C@H](NC(=O)NC=2C=CC(Cl)=CC=2)[C@@H](C)OC)CC1 ZWZDESFYXWGAAO-UOHPHXQYSA-N 0.000 claims description 2
- KPYMDLGMKCHCBI-KXBFYZLASA-N 1-(4-chlorophenyl)-3-[(2s,3s)-3-hydroxy-1-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-1-oxobutan-2-yl]urea Chemical compound N([C@@H]([C@@H](O)C)C(=O)N1CCN(CC1)C1CCN(C)CC1)C(=O)NC1=CC=C(Cl)C=C1 KPYMDLGMKCHCBI-KXBFYZLASA-N 0.000 claims description 2
- XIXATPKQPWDLNM-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[1-(4-hydroxyphenyl)-2-oxo-2-(4-piperidin-1-ylpiperidin-1-yl)ethyl]urea Chemical compound C1=CC(O)=CC=C1C(C(=O)N1CCC(CC1)N1CCCCC1)NC(=O)NC1=CC=C(Cl)C=C1 XIXATPKQPWDLNM-UHFFFAOYSA-N 0.000 claims description 2
- RCBKLOFIRPSRII-XMMPIXPASA-N 1-[(1r)-2-(4-benzylpiperazin-1-yl)-2-oxo-1-phenylethyl]-3-(4-chlorophenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCN(CC=2C=CC=CC=2)CC1 RCBKLOFIRPSRII-XMMPIXPASA-N 0.000 claims description 2
- OTUAYANRALSULO-SQJMNOBHSA-N 1-[(1r)-2-[(3s)-3-benzylpiperidin-1-yl]-2-oxo-1-phenylethyl]-3-(4-chlorophenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1C[C@H](CC=2C=CC=CC=2)CCC1 OTUAYANRALSULO-SQJMNOBHSA-N 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- BKJXQOQIIKSWTK-BOXHHOBZSA-N 1-(4-chlorophenyl)-3-[(1r)-2-(4-cyclohexylpiperazin-1-yl)-2-oxo-1-thiophen-2-ylethyl]urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(Cl)=CC=C1NC(=O)N[C@@H](C=1SC=CC=1)C(=O)N1CCN(C2CCCCC2)CC1 BKJXQOQIIKSWTK-BOXHHOBZSA-N 0.000 claims 1
- NJIHLBDFWIDERD-KXTRFFEISA-N 1-(4-chlorophenyl)-3-[(1r)-2-[5-(4-fluorophenyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-oxo-1-phenylethyl]urea Chemical compound C1=CC(F)=CC=C1N1C(CN2C(=O)[C@H](NC(=O)NC=3C=CC(Cl)=CC=3)C=3C=CC=CC=3)CC2C1 NJIHLBDFWIDERD-KXTRFFEISA-N 0.000 claims 1
- YMGZBKVEGYJSGW-JOCHJYFZSA-N 1-(4-chlorophenyl)-3-[(1r)-2-oxo-1-phenyl-2-(4-pyridin-2-ylpiperazin-1-yl)ethyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)N[C@H](C=1C=CC=CC=1)C(=O)N1CCN(C=2N=CC=CC=2)CC1 YMGZBKVEGYJSGW-JOCHJYFZSA-N 0.000 claims 1
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- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Veterinary Medicine (AREA)
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- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE10358539A DE10358539A1 (de) | 2003-12-15 | 2003-12-15 | Carbonsäureamidderivate |
DE10358539.7 | 2003-12-15 | ||
PCT/EP2004/013202 WO2005056528A1 (de) | 2003-12-15 | 2004-11-19 | Carbonsäureamidderivate |
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CA2549548A1 true CA2549548A1 (en) | 2005-06-23 |
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EP (1) | EP1694643A1 (pt) |
JP (1) | JP4990627B2 (pt) |
KR (1) | KR20060123305A (pt) |
CN (1) | CN1890216A (pt) |
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AU (1) | AU2004296956B2 (pt) |
BR (1) | BRPI0417153A (pt) |
CA (1) | CA2549548A1 (pt) |
DE (1) | DE10358539A1 (pt) |
RU (1) | RU2006125380A (pt) |
WO (1) | WO2005056528A1 (pt) |
ZA (1) | ZA200605839B (pt) |
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JP4769082B2 (ja) * | 2003-12-17 | 2011-09-07 | 武田薬品工業株式会社 | ウレア誘導体、その製造法及び用途 |
US7678913B2 (en) | 2004-12-07 | 2010-03-16 | Portola Pharmaceuticals, Inc. | Ureas as factor Xa inhibitors |
US7601844B2 (en) * | 2006-01-27 | 2009-10-13 | Bristol-Myers Squibb Company | Piperidinyl derivatives as modulators of chemokine receptor activity |
TWI433838B (zh) | 2008-06-25 | 2014-04-11 | 必治妥美雅史谷比公司 | 作為趨化因子受體活性調節劑之六氫吡啶衍生物 |
US8642622B2 (en) | 2010-06-16 | 2014-02-04 | Bristol-Myers Squibb Company | Piperidinyl compound as a modulator of chemokine receptor activity |
EP2646030A1 (en) | 2010-12-03 | 2013-10-09 | Allergan, Inc. | Pharmaceutical compositions comprising 3,4- dihydroisoquinolin-2(1 h)-yl-3-phenylurea derivatives having formyl peptide receptor like-1 (fprl-1) agonist or antagonist activity |
FR2985256B1 (fr) * | 2011-12-30 | 2016-03-04 | Pitty Marc Henry | Derives piperazinyles pour le traitement de cancers |
CN111372576A (zh) | 2017-11-17 | 2020-07-03 | 塞尔利克斯生物私人有限公司 | 用于治疗眼部病症的组合物和方法 |
WO2022221686A1 (en) * | 2021-04-15 | 2022-10-20 | Pardes Biosciences, Inc. | Inhibitors of cysteine proteases and methods of use thereof |
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JPH0655758B2 (ja) * | 1984-08-24 | 1994-07-27 | 味の素株式会社 | アミノ酸誘導体 |
US5346907A (en) * | 1988-04-05 | 1994-09-13 | Abbott Laboratories | Amino acid analog CCK antagonists |
US5721251A (en) * | 1993-12-10 | 1998-02-24 | Merck & Co., Inc. | Piperidine, pyrrolidine and hexahydro-1H-azepines promote release of growth hormone |
IL115420A0 (en) * | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
JPH09227523A (ja) * | 1996-02-26 | 1997-09-02 | Toubishi Yakuhin Kogyo Kk | セリンから誘導される抗cck活性化合物 |
US5847148A (en) * | 1997-04-10 | 1998-12-08 | Pharmacia & Upjohn Company | Thiadiazole derivatives useful for the treatment of diseases related to connective tissue degradation |
DE10063008A1 (de) * | 2000-12-16 | 2002-06-20 | Merck Patent Gmbh | Carbonsäureamidderivate |
AU2002322585A1 (en) * | 2001-07-20 | 2003-03-03 | Adipogenix, Inc. | Fat accumulation-modulating compounds |
EP1499607B1 (en) * | 2001-12-04 | 2005-12-07 | Actelion Pharmaceuticals Ltd. | 4-(piperidyl- and pyrrolidyl-alkyl-ureido)-quinolines as urotensin ii receptor antagonists |
AU2002359458A1 (en) * | 2001-12-12 | 2003-06-23 | Eli Lilly And Company | Alanyl-piperidine heterocyclic derivatives useful against cardiovascular diseases |
EP1499591A1 (de) * | 2002-04-27 | 2005-01-26 | MERCK PATENT GmbH | Carbonsäureamide als inhibitoren des koagulationsfaktors xa |
US7220862B2 (en) * | 2002-06-05 | 2007-05-22 | Bristol-Myers Squibb Company | Calcitonin gene related peptide receptor antagonists |
DE10302500A1 (de) * | 2003-01-23 | 2004-07-29 | Merck Patent Gmbh | Carbonsäureamidderivate |
US6846836B2 (en) * | 2003-04-18 | 2005-01-25 | Bristol-Myers Squibb Company | N-substituted phenylurea inhibitors of mitochondrial F1F0 ATP hydrolase |
BRPI0414777A (pt) * | 2003-09-26 | 2006-11-21 | Actelion Pharmaceuticals Ltd | compostos, composições farmacêuticas, uso de um ou mais compostos, e, método de tratar um paciente que sofre de um distúrbio |
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2003
- 2003-12-15 DE DE10358539A patent/DE10358539A1/de not_active Withdrawn
-
2004
- 2004-11-19 CN CNA2004800365005A patent/CN1890216A/zh active Pending
- 2004-11-19 WO PCT/EP2004/013202 patent/WO2005056528A1/de active Application Filing
- 2004-11-19 US US10/582,850 patent/US7951804B2/en not_active Expired - Fee Related
- 2004-11-19 CA CA002549548A patent/CA2549548A1/en not_active Abandoned
- 2004-11-19 RU RU2006125380/04A patent/RU2006125380A/ru not_active Application Discontinuation
- 2004-11-19 KR KR1020067011538A patent/KR20060123305A/ko not_active Application Discontinuation
- 2004-11-19 AU AU2004296956A patent/AU2004296956B2/en not_active Ceased
- 2004-11-19 EP EP04820053A patent/EP1694643A1/de not_active Withdrawn
- 2004-11-19 BR BRPI0417153-5A patent/BRPI0417153A/pt not_active Application Discontinuation
- 2004-11-19 JP JP2006544246A patent/JP4990627B2/ja not_active Expired - Fee Related
- 2004-12-15 AR ARP040104655A patent/AR047850A1/es unknown
-
2006
- 2006-07-14 ZA ZA200605839A patent/ZA200605839B/en unknown
Also Published As
Publication number | Publication date |
---|---|
ZA200605839B (en) | 2007-10-31 |
JP2007513987A (ja) | 2007-05-31 |
BRPI0417153A (pt) | 2007-03-06 |
RU2006125380A (ru) | 2008-01-27 |
CN1890216A (zh) | 2007-01-03 |
JP4990627B2 (ja) | 2012-08-01 |
KR20060123305A (ko) | 2006-12-01 |
AR047850A1 (es) | 2006-03-01 |
DE10358539A1 (de) | 2005-07-07 |
AU2004296956A1 (en) | 2005-06-23 |
US7951804B2 (en) | 2011-05-31 |
EP1694643A1 (de) | 2006-08-30 |
US20070123509A1 (en) | 2007-05-31 |
WO2005056528A1 (de) | 2005-06-23 |
AU2004296956B2 (en) | 2010-11-11 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
FZDE | Discontinued |
Effective date: 20121119 |